1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59596660、化合物

HRID 2264966ノート

反応式

HRID 2264966 の反応式
[Na+].[F:2][C:3]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]1[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:14]=2[N:13]([CH3:20])[C:12]=1[C:21]([O-:23])=O.[Si:24]([O:31][C@@H:32]([CH3:36])[CH2:33][O:34][NH2:35])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[Si:24]([O:31][C@@H:32]([CH3:36])[CH2:33][O:34][NH:35][C:21]([C:12]1[N:13]([CH3:20])[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[C:11]=1[NH:10][C:4]1[CH:5]=[CH:6][C:7]([I:9])=[CH:8][C:3]=1[F:2])=[O:23])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 58374418(S)-O-(2-((tert-Butyldimethylsilyl)oxy)propyl)hydroxylamineHCID 67212115HCID 67212115、化合物

生成物 1

HCID 59596660HCID 59596660、化合物収率 62.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-(2-Fluoro-4-iodo-phenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid sodium salt (0.20 g, 0.46 mmol), O—[(S)-2-(tert-butyldimethylsilanyloxy)-propyl]-hydroxylamine (95 mg, 0.46 mmol), HOBT (69 mg, 0.51 mmol), EDCI (97 mg, 0.51 mmol) and DIPEA (0.08 ml, 0.46 mmol) were suspended in a mixture of THF (3 ml) and DMF (1 ml). The reaction was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (20 ml) and washed with aqueous saturated sodium bicarbonate solution (20 ml). The aqueous layer was isolated and extracted with ethyl acetate (2×10 ml) and the combined organic layers dried, washed with brine and dried over magnesium sulfate before concentrating in vacuo. The crude residue was purified by flash chromatography (SiO2, gradient 1-3% methanol in dichloromethane) to yield the title compound as an off-white solid (171 mg, 62%). LCMS (method B): RT=3.00 min, M+H+=599.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (20 ml)
  3. washwashed with aqueous saturated sodium bicarbonate solution (20 ml)
  4. customThe aqueous layer was isolated
  5. extractionextracted with ethyl acetate (2×10 ml)
  6. customthe combined organic layers dried
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationbefore concentrating in vacuo
  10. customThe crude residue was purified by flash chromatography (SiO2, gradient 1-3% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-39e88634122a43d4807db7cb4a10b53a
出典データセット
uspto-grants-2010_12
特許番号
US07855216B2

反応ノート

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